JP5960683B2 - 殺真菌剤としてのケトヘテロアリールピペリジンおよび−ピペラジン誘導体 - Google Patents

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Publication number

JP5960683B2

JP5960683B2 JP2013506638A JP2013506638A JP5960683B2 JP 5960683 B2 JP5960683 B2 JP 5960683B2 JP 2013506638 A JP2013506638 A JP 2013506638A JP 2013506638 A JP2013506638 A JP 2013506638A JP 5960683 B2 JP5960683 B2 JP 5960683B2

Authority

JP

Japan

Prior art keywords

alkyl

cycloalkyl

substituents

haloalkyl

phenyl

Prior art date

2010-04-28

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 12
• 239000000417 fungicide Substances 0.000 title description 7
• -1 1, 2, 3, 4-tetrahydronaphthalen-1-yl Chemical group 0.000 claims description 565
• 150000001875 compounds Chemical class 0.000 claims description 300
• 238000000034 method Methods 0.000 claims description 176
• 125000001424 substituent group Chemical group 0.000 claims description 138
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical class [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 113
• 239000000203 mixture Substances 0.000 claims description 88
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 67
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 40
• 241000233866 Fungi Species 0.000 claims description 38
• 229910052757 nitrogen Inorganic materials 0.000 claims description 38
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 37
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 35
• 229910052799 carbon Inorganic materials 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 33
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 31
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 28
• 239000000460 chlorine Substances 0.000 claims description 27
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 27
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 26
• 229910052801 chlorine Inorganic materials 0.000 claims description 26
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 23
• 229910052794 bromium Inorganic materials 0.000 claims description 23
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 23
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
• 230000003032 phytopathogenic effect Effects 0.000 claims description 22
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 21
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 21
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
• 239000011737 fluorine Substances 0.000 claims description 21
• 229910052731 fluorine Inorganic materials 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 19
• 230000009261 transgenic effect Effects 0.000 claims description 19
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 18
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 17
• 150000002431 hydrogen Chemical group 0.000 claims description 17
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 14
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 14
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 11
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 10
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 10
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 10
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 9
• 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 8
• 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 8
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 8
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 8
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 8
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 8
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 8
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 239000004094 surface-active agent Substances 0.000 claims description 8
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 8
• 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims description 7
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 7
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 7
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 7
• 125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 claims description 7
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
• 125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 claims description 7
• 125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 claims description 7
• 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims description 7
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 7
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 7
• 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 7
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 7
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 7
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 6
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 6
• 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 claims description 6
• 125000004043 oxo group Chemical group O=* 0.000 claims description 6
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 6
• 239000011593 sulfur Substances 0.000 claims description 6
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 6
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 5
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
• 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 claims description 5
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 5
• 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims description 5
• 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 5
• 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 5
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 239000004067 bulking agent Substances 0.000 claims description 5
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 5
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 4
• 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 4
• 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 4
• 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 4
• MGHNDJJPPOAIHK-UHFFFAOYSA-N 1H-inden-1-yl Chemical group C1=CC=C2[CH]C=CC2=C1 MGHNDJJPPOAIHK-UHFFFAOYSA-N 0.000 claims description 4
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 4
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
• 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 claims description 4
• QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 4
• 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 4
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 4
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 4
• 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 claims description 3
• 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 3
• 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 claims description 3
• 125000004227 1,3-benzoxazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)OC2=C1[H] 0.000 claims description 3
• 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 3
• 125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 claims description 3
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 3
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 3
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 3
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 3
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000004536 indazol-1-yl group Chemical group N1(N=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000004245 indazol-3-yl group Chemical group [H]N1N=C(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 3
• 125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims description 3
• 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 3
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 3
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 3
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 3
• 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 claims description 3
• 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 claims description 3
• 238000002156 mixing Methods 0.000 claims description 3
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
• 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 3
• 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 3
• 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 3
• 125000004747 1,1-dimethylethoxycarbonyl group Chemical group CC(C)(OC(=O)*)C 0.000 claims description 2
• 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 claims description 2
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
• 150000001721 carbon Chemical group 0.000 claims description 2
• CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
• 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 2
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 2
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
• 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 2
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
• 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 2
• 238000006467 substitution reaction Methods 0.000 claims description 2
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
• 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims 2
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 2
• NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims 1
• 125000000262 haloalkenyl group Chemical group 0.000 claims 1
• 241000196324 Embryophyta Species 0.000 description 234
• 230000008569 process Effects 0.000 description 85
• 238000006243 chemical reaction Methods 0.000 description 84
• 108090000623 proteins and genes Proteins 0.000 description 57
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
• 239000011541 reaction mixture Substances 0.000 description 37
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
• 239000002253 acid Substances 0.000 description 36
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
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